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Design, Synthesis and Biological Evaluation of Novel Piperazine Derivatives as CCR5 Antagonists

Figure 6

Synthesis of target piperazine derivatives 23a–h.

Reagents and conditions: a) SOCl₂, EtOH, 0°C, 0.5 h, rt, 3 h, reflux, 1 h; b) (Boc)₂O, NaOH, H₂O, Dioxane, rt, 12 h; c) DIBAL-H, CH₂Cl₂, −78°C, 3 h; d) NaBH(OAc)₃, CH₂Cl₂, rt, 8 h; e) 6NHCl, EtOAc, rt, 3 h; f) EDC.HCl, CH₂Cl₂, rt, 6 h.

doi: https://doi.org/10.1371/journal.pone.0053636.g006